Top 10 kids-friendly things to do in Annapolis

1. Outdoor watercolor painting class in Annapolis

Two hours of outdoor painting instruction — learn watercolor techniques while capturing iconic sailboats in the historic district of Annapolis, led by an award-winning local artist.

2. Interactive walking scavenger hunt in Annapolis

Flexible self-guided walking tour—explore historic stories, solve riddles, and enjoy architecture throughout Annapolis at your own pace using a mobile app.

3. Private cultural walking tour of historic Annapolis

Two hours of flat walking — explore historic Annapolis waterfront with a focus on culture and storytelling from local history.

4. Historic walking tour of Annapolis' harbor and colonial downtown

Two-hour walking tour covering Annapolis' harbor, Georgian mansions, and the Maryland State House, led by an engaging guide with personal stories.

“My wife and I arranged a private walking tour with Michael, which turned out to be the best part of our visit to Annapolis. The outstanding reviews are accurate! His tour of the Naval Academy and historic downtown was a wonderful mix of history, interesting facts, and enjoyment. Michael is an excellent guide, and we strongly suggest him to anyone coming to Annapolis for the first time.”— Q7841VKjamesw

5. Outdoor painting class in Annapolis with a local artist

Two hours of outdoor painting in the historic district of Annapolis, led by an award-winning watercolorist.

“This is an excellent opportunity to immerse yourself in the charm of Annapolis' old town, appreciating its architecture and history while exploring sketching and watercolors. The teacher is very patient and tailored their approach to each student's skill level. Inspiring and engaging — truly a must-do.”— Blanche_M

6. Urban sketching and painting class in Annapolis

Three-hour outdoor painting session — learn from an award-winning local artist while capturing the architecture of Annapolis' historic district.

“I had a fantastic time. Em was an excellent instructor who made me feel at ease despite my lack of art experience. She was also very engaging in conversation. I highly recommend this activity.”— Sam_E

7. Historic pub crawl in Annapolis: tales of scandal and intrigue

Two hours of bar-hopping (approx. 0.5 miles) — visit three local taverns while hearing stories of Annapolis' scandalous past and colorful history, adults only.

“Baltimore Tours and Crawls originated in Annapolis, so their expertise is evident. They provide a variety of engaging tours in the Fells Point area, including the Walking Ghost Tour, Haunted Pub Crawl, Twisted History Tour, Bootleggers & Rum Runners Tour, and the Sports Legends Tour. Each tour caters to different interests—historical, supernatural, athletic, and quirky stories. Departing from the historic Admiral Fells Inn around 8 PM, these tours last about 90 minutes. The Pub Crawl is particularly enjoyable if you’re not driving. The guides are highly knowledgeable and entertaining, having earned the title of "Best Downtown Tour" in Fells Point for three consecutive years. Dogs are welcome as long as they are leashed and friendly.”— Steve C

8. Historic Annapolis walking tour with a small group

Two hours, 2 miles of walking through Annapolis — guided small group setting at a relaxed pace, rain or shine, with frequent stops.

“As a resident, I'm familiar with much of what was shared, yet I still discover new aspects of my hometown on tours like this. My friend visiting from out of town, who had never experienced Annapolis before, also found the tour enjoyable. Our guide, Rebecca, mentioned she was a local, but both she and her partner frequently mispronounced Roger Taney's name; Marylanders pronounce it as "tawney." It wasn't a major issue, but it did make me curious.”— fiedhp

9. Annapolis Ghost Tour — a 90-minute evening walking tour

Ninety minutes in historic downtown Annapolis, led by a local historian, exploring haunted sites and captivating ghost stories.

“Ev did an exceptional job on our tour! She guided us to several of her favorite haunted spots in historic Annapolis. Her energy was fantastic, and she transported us back in time with her stories of horror and lost love as we walked the streets.”— scotc2017

10. App-led scavenger hunt through Annapolis

Two to three hours exploring Annapolis—iconic landmarks, trivia questions, and team challenges with an interactive app experience.

“I couldn't figure out how to get started. The instructions were not helpful, and when I attempted to follow them, I was informed that my tickets had already been redeemed. I hope to receive a refund.”— emilydW4880IT